Collect. Czech. Chem. Commun. 1986, 51, 459-477

9-(Aminoalkyl)-8-hydroxyadenines: Preparation, mechanism of formation and use in affinity chromatography of S-adenosyl-L-homocysteine hydrolase

Antonín Holý, Jitka Kohoutová, Aleš Merta and Ivan Votruba

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Bromine reacts with 9-(2-hydroxyethyl)- (Va), 9-(3-hydroxypropyl)- (Vb), 9-(2-hydroxypropyl)- (Vc), 9-(2,3-dihydroxypropyl)- (Vd), 9-(1,3-dihydroxy-2-propyl)- (Ve), 9-threo-(2,3-dihydroxybutyl)- (Vf) and 9-threo-(2,3,4-trihydroxybutyl)adenine (Vg) to give 8-bromoadenine derivatives (Vl). Reaction of compounds Vl with ammonia results in intramolecular cyclization to five- and six-membered cyclic esters which are regiospecifically opened to afford the respective 2-amino-alkyl-8-hydroxyadenines (VIIa, b) and 3-aminoalkyl-8-hydroxyadenines (VIIc-VIIf). Binding of compounds VII to CH-Sepharose 4B led to the polymeric material XIII capable of binding S-adenosyl-L-homocysteine hydrolase. Compounds XIII derived from the amino derivatives VIIa, b, d are of affinity support character and liberate the enzyme only on elution with dilute adenosine solution.